Sodium Hydroxide → HCID 59715022, compound

Participants

Reaction Steps

Lithium aluminum hydride (172 mg) was suspended in tetrahydrofuran (10 mL). To this was added a solution of dimethyl 5-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]isophthalate (synthesized in Example 24) (1.30 g) in tetrahydrofuran (15 mL) dropwise at room temperature. The suspension was stirred for 3 hours. Water (0.16 mL) was added to the suspension and it was stirred for 10 minutes. A 15% aqueous sodium hydroxide solution (0.16 mL) was added to the suspension and it was stirred for 15 minutes. Diethyl ether was added to the mixture, followed by addition of water (0.48 mL). The solution was stirred for 30 minutes. The solution was dried over anhydrous magnesium sulfate, filtered and the filtrate was then concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, ethyl acetate] to give the title compound (1.04 g).

Provenance & Evidence